Book Club Discussion Questions for Fair Rosaline by Natasha Solomons

1. What are Rosaline's objections to entering the convent? Do you think any path open to a woman of her class at her time would have given her the things that she wants?
2. How do you think the feud between the Montagues and Capulets colors Rosaline and Romeo's early interactions? How does she feel about keeping their identities secret while out together and the truth of their relationship to herself?
3. Romeo seduces vulnerable young women, like servants, as well as daughters of the upper class, like Rosaline and Juliet. What do you feel he wants from them? Does it differ by rank? How does Rosaline disappoint those expectations?
4. What do you believe Rosaline hopes to gain by telling Tybalt about her relationship with Romeo? Do you think she did the right thing in telling him, even though it led to his death? What would you have done in her place?
5. Rosaline struggles to get Juliet to see the danger that she is in and knows that she was just as stubborn when she was in Juliet's position. Can you think of a character whose advice either of the girls might have respected?
6. What role does pride play in the book? In what scene do you feel a character's pride causes the most harm?
7. How do Paris and Romeo compare in their pursuit of Juliet? Do you think their goals are the same or different? Do you agree with Rosaline that Juliet's parents are to blame for the way the two men made a victim of Juliet?
8. At the beginning of the book, Rosaline's freedom is the virtue she holds most dear. By the end she sacrifices it to earn the abbess's help. What changed for her? For whom would you make a similar sacrifice?
9. What do you think of the author's interpretation of the tale of star-crossed lovers? What feature did you like most about her take on the story? Did Fair Rosaline change your interpretation of Romeo and Juliet at all? What about the author's note?
10. Fair Rosaline is, at its heart, historical fiction. Did you learn anything new about the time period in which the story is set?
11. Why do you suppose Rosaline's mother wanted her to go to a convent? Why do you think she didn't tell Rosaline before her death?
12. Masetto wants to send Rosaline to the convent right way, while Rosaline requests freedom first. Which do you believe to be the better approach to a life-altering event?
13. Rosaline tells Romeo that he "cannot tilt at fate," he'll lose. How large a role, do you think, does fate play in the story? How much of what occurs is by design? How much a part does fate plays in your own life, in your opinion?
14. Romeo demands that Rosaline choose to love him. She'd believed that "love was something that happened without one's choosing; it was unconscious and inevitable." What's your opinion about love? Do you believe it can be chosen, or is it always random?
15. Do you feel Rosaline would have been enamored of Romeo if she wasn't slated for the convent, or would she have been better able to resist his charms?
16. Do you think Romeo had feelings for Juliet, or was he simply an opportunist?
17. When she reads the list of names Rosaline gives her, the mother abbess says, "I sense another plague coming to the wicked men of Verona." What was your reaction to this statement?
18. Do you think Rosaline and Juliet will be happy, living out their lives in the convent? Why or why not?

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Unless otherwise stated, this discussion guide is reprinted with the permission of Sourcebooks Landmark. Any page references refer to a USA edition of the book, usually the trade paperback version, and may vary in other editions.